


If you Wanna be a Party Animal, Then you Gotta Learn to Live in the Jungle

by badwolfchild



Series: I'm a Book Half Unread [10]
Category: Gilmore Girls
Genre: Alternate Universe - Canon Divergence, F/M, Families of Choice, Fatherly Luke, M/M, Underage Drinking
Language: English
Status: Completed
Published: 2019-02-10
Updated: 2019-02-10
Packaged: 2019-10-25 22:42:52
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 10,676
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17734037
Author URL: https://archiveofourown.org/users/badwolfchild/pseuds/badwolfchild
Summary: Jess deals with the fallout of his New York trip, bonds with Emily of all people over being outsiders, and goes on a group date with Dean and his new girlfriend along with Rory. What could go wrong?Somewhere along the way he also gets in a crossword fight with Taylor Doose.





	If you Wanna be a Party Animal, Then you Gotta Learn to Live in the Jungle

**Author's Note:**

> Title from the Bastille song Good Grief.
> 
> So with all of winter being packed into the last week for me, and catching a cold, I got a lot of writing done very quickly. 
> 
> The next few installments are going to be a little lighter to make up for all the heavy drama Jess has been put through lately. I thought he deserved a break. I'm still always up for suggestions, so don't be shy. I love reading what you think should happen next, or even just what you think so far.
> 
> Anyway, I hope everyone enjoys this newest installment!

After Jess got back from his “Mr. Toad’s Wild Ride, New York Edition” as Lorelai called it, then his not-so-minor breakdown with Luke and Lorelai, he thought his uncle would go easy on him and figure Jess had punished himself enough all on his own.

 

He was wrong.

 

Once Jess got settled back home, Luke laid down the law. He’s grounded for the entirety of the month of December, including New Years day. There are only three places he’s allowed for the month; school, where Lane will walk with him from the diner and back, the diner, where he has to stay downstairs with Luke the whole time, and the Inn, where Lorelai will drive him to and from. He also has to go wherever Luke goes like he’s some little kid, be it the grocery store, bank, or town meetings, if Luke’s going so is he. No tv, no music, no phone, and the only books he can read are his textbooks and whatever book they’re reading for his english class at the time, which he’s going to verify with Lane. So in other words, it’s going to be the most mind-numbingly, boring month of his life, but he’ll grit through it, if only so he doesn’t let Luke down again.

 

God, he’s felt like shit from the way he treated him and Lorelai, disappointing them like he had. Taking off to another state without so much as a note, talking Oliver into going, then shaming him when he found out he had called Lorelai. He was such a jerk. He still remembers all the horrible things he had said when he was drunk. Luke took pity on him, Lorelai probably having filled in the blanks for him at some point, and made an exception with the phone rule so he could call Oliver and apologize.

 

He never answered. Jess has called him every night, but only ever gets his answering machine. He says the same thing every time, apologizing and begging him to please just call him back.

 

It doesn’t help that Dean has been avoiding him at every turn. Ever since the great Rory/Dean breakup, Dean has been eating lunch with his old sports buddies. Sure, Jess has Lane and Dave at lunch, but he barely knows Dave and he mostly feels like a third wheel between the two as they make googly eyes at each other. It never bothered him much before, since him and Dean would roll their eyes at them and fake gag until Lane threw whatever soy/tofu thing her mother had packed for her, but now he’s just the odd one out at the table.

 

The only class he shares with Dean is gym, but every time he tries to talk to him, the guy just sprints way ahead of him, knowing Jess could never keep up. It sucks. It really sucks. And he’s had just about enough of it.

 

They’re all out on the field today, freezing their asses off since the gym is closed from some ant infestation again. There are a few students trying to play soccer, something made difficult due to all the snow on the ground. Jess has seen people kick clumps of ice by mistake more than the actual ball.

 

Spotting Dean as one of the few trying to play, something in Jess just snaps. Marching up to him, he grabs his shoulder and forces him to spin around.

 

“Hey!”

 

“Jess, I'm not looking for a fight.” He tries to get away, but Jess doesn't let him.

 

“Too bad. Now would you stop treating me like I'm some leper?” 

 

By now, everyone is watching the two of them, including the ones that were trying to play. “I don't know what you're talking about. Can you let us get back to our game now?”

 

A sudden thought occurs to Jess. What if Dean was only his friend because Rory wanted him to. Now that him and Rory are broken up, there's no reason for Dean to want anything to do with him. In a rage, Jess charges at his back, tackling Dean to the ground. They roll around the snow and dirt, Dean strictly on the defence as Jess tries, and fails, to nail him in the face. “You asshole!”

 

“What the hell, Jess!?” Dean manages to get the upper hand, spinning Jess around and pinning a struggling Jess to the ground.

 

Before Jess gets the chance to say anything else, the two get torn apart by the coach and Lane, the only two people not frozen in shock. “Mariano, Forester, office! Now!”

 

0000000000000000000000

 

Jess and Dean sit on a bench outside the principal's office as the coach is inside explaining the situation.

 

“What's your problem?” Dean grumbles, tenderly pressing one of the bruises on his arms.

 

“Don't talk to me.” Stupid coach, not even letting them change. Now they’re stuck in their stupid gym clothes for the foreseeable future.

 

Dean sighs, forgetting his arm. “Seriously, man? You tackle me out of nowhere and you're not even gonna tell me why?”

 

“You know why.” Jess picks at his nails, chunks of dirt stuck under them.

 

“No, I don't! Is it because Rory and I broke up? Because that wasn't just on me, it was a mutual break up.”

 

“I don't care if she was the one that dumped your ass! I'm just freakin’ pissed that you don't even have the guts to tell me to my face that this whole thing was for her!” Jess snaps, the secretary giving him a sharp look. He waves her off, signaling that he sees her and will lower his voice.

 

Dean blinks, sputtering. “Thing? What thing was for her? Wait, do you think I'm only friends with you because of her?” Jess crosses his arms, kicking a foot out. “Do you have brain damage or something?” Dean scoffs.

 

“Yeah, sure, laugh it up. Then why the hell have you been avoiding me ever since the two of you broke up?”

 

Dean shakes his head, growing serious. “Jess, I thought  _ you _ were mad at  _ me.” _ Jess finally glances at him, raising a brow. “Rory's like your sister, dude, I thought you'd want to defend her honor or something.”

 

“No wonder you two didn't work out. Anyone who just met Rory knows she doesn't need anyone to defend her, she can do it all herself.” Jess feels a smirk grow on his face. “Frankly, you assuming that makes you sound a little sexist. Although, Donna Reed would love having a man defend her.”

 

Dean shoves him with a laugh of his own. “Shut up. Who told you about that damn Donna Reed fiasco?”

 

“Lorelai and Rory.”

 

Dean rolls her eyes. “Of course they did.” He mutters under his breath.

 

“Did-” Jess snorts, holding back his laughter. “Did you really ‘Do the man's part’ and take out the trash?” 

 

“Can we go back to you giving me the cold shoulder, I think I'd prefer that right about now.”

 

“And the dress. Big, poofy dress that could sweep a whole sidewalk of people down in one fell swoop. Oh! And I almost forgot about the pearls! And-”

 

“Alright, I get it, I was actually there if you'll recall.”

 

“And yet you didn't get a single picture of the evening.” Dean gives him another shove, still chuckling.

 

000000000000000000000000

 

Jess gives his escort a wave, walking into the diner. Before he even knows what's going on, Luke grabs a handful of his shirt and drags him to the storeroom. 

 

“Ow, ow, you're pinching! Would you quit?”

 

Luke drops him, taking deep breaths and pinching the bridge of his nose. “So, I got an interesting call from your school today.”

 

Jess straightens out his shirt. “Yeah? They finally letting you go back? Because I gotta say, with the age difference between you and everyone else, it'll be a little weird.”

 

“A fight?! Are you serious?! Who did you get in a fight with?!”

 

“Dean.” He admits reluctantly.

 

“Dea-” Luke purses his lips. “That's it. You and Rory are not seeing him again. He's nothing but trouble for the two of you.”

 

“Luke, it was just a misunderstanding. We're fine now.”

 

“A misunderstanding?” Luke asks skeptically.

 

“Yes, and we're fine now. Can I go? Me and the front counter have a hot date planned.” He tries to escape, but gets stopped by Luke grabbing his shirt again.

 

“Whoa, not so fast there, speed racer. What misunderstanding?”

 

Jess groans. “Would you quit it? I happen to like this shirt.”

 

“Then you shouldn't have rolled around in the mud with Dean in it. Now what was the misunderstanding about?”

 

“Nothing. And for the record, I was wearing my gym clothes, so those are gonna need a washing tonight.” Luke stares him down, causing him to shift. “Fine. He was avoiding me because he thought I was automatically going to take Rory's side of the break up, and I thought he was avoiding me because he was only my friend because Rory was making him.  _ Now _ can I go?”

 

Luke sighs. “Alright, go buss some tables for a bit. But your grounding just got extended until January 8th for the fighting.”

 

“Lu-”

 

“Wanna make it two weeks?”

 

“Ugh, I didn't realize I was living in communist Russia. One week and the democracy deal has already fallen through.”

 

“Go!” He points.

 

000000000000000000000

 

Jess starts getting restless as his winter break approaches. Two weeks and he still hasn't heard a word from Oliver. He tried having Rory send a message to him when she was in the diner one morning, but she refused, not wanting to get in the middle of their fight. 

 

Him and Oliver had plans to hang out during the break. They were going to compete against Rory and Lorelai in the snowman building contest, mock  _ every _ Christmas movie they could get their hands on (which Oliver had admitted included  _ Die Hard. _ Ha! In your face Rory!), and just spend every moment they could together without school getting in the way.

 

“Hey, Luke?” Jess asks from what's now become his spot at the counter, plan starting to form.

 

“Yeah, what is it?” Luke asks, distracted as he passes by with some plates.

 

“You know how I've been complaining about needing to run my car so the cold doesn't completely kill it? Well, I’ve been thinking-”

 

“That's never a good sign.” Luke says as he snorts.

 

“I've been  _ thinking,  _ and I’ve come up with something that's a bit of a win-win.” Luke stops, giving him his full attention. “You should let me go pick up Rory from Chilton, that way she saves on bus fare, and I get to get my car running. If I leave now, I'll be there right on time to catch her as she leaves from working on the Franklin.”

 

“Fine.”

 

“Wait, really?” This is way too easy.

 

Luke shrugs, wiping the counter. “Sure, you made some good points there, and it saves me from having to drive that rust bucket of yours to keep that engine puttering along. One condition though.” Jess knew there was going to be a catch. “You go straight there and back, no detours. When you get back, bring Rory-”

 

“Here to verify, yeah, I get it. Can I go now?”

 

“Fine, scram. Be careful though! The roads are icy!”

 

“Will do, I'll be back soon.” He rushes to get his leather jacket on, already out the door before Luke changes his mind.

 

000000000000000000000

 

Jess gets there a little early. Nerves setting in, he sits on his trunk, fiddling with an unlit cigarette. Noticing some people coming out, he straightens up, looking for Rory and Oliver. After most people pass, he finally spots Rory and Oliver chatting as they leave along with Paris. Great, just the person he wanted to avoid.

 

“Hey.” He gets their attention, stuffing the cigarette back in his pocket as he jumps down.

 

Oliver keeps his face blank, but Jess can tell by the way he's gripping the strap to his messenger bag that he's not happy to see him. Paris marches forward, getting in his face. “What are doing here, Bukowski? I heard all about your Jack Kerouac moment, so you have some nerve showing your face here.”

 

“This has nothing to do with you, Austen.” He tries to brush her off.

 

“You put one of my best writers at risk, so yeah, it has everything to do with me.” She blocks his path again.

 

Jess is really trying to keep his temper in check, but Paris is making it difficult with all her Parisness. Before he snaps at her to back off, Oliver steps forward. “Paris, it's fine. You can go.”

 

“But-” Oliver gives her a look, which causes her to sigh. “Watch yourself.” She points at Jess.

 

“I'll be on my best behavior.”

 

She gives him one more searching look before nodding and taking off. “I'll, um, go wait in the car.” Rory awkwardly walks off, getting in the front seat, leaving Jess and Oliver alone.

 

“Hey.” Jess swallows, mouth suddenly dry.

 

“Hey.” Oliver parrots back, staying put.

 

Jess scratches the back of his head to give his hands something to do other than shake. “Look, I don't know if you got my messages, but I'm sorry for how I acted that night. I was a real dick.”

 

“Yes, you were.” Oliver agrees. 

 

“I was drunk and said some terrible things, to you especially.”

 

“I was just trying to help. Drunk or not, I never deserve to be spoken that way to.”

 

Jess nods, biting his lip. “I know, hence the me being a dick. I'm sorry.”

 

“So you've said.” Oliver doesn't budge. “But how do I know you’re not going to lash out at me next time?”

 

“There won't be a next time, I swear.” Jess says firmly. He'll make sure of that.

 

“But how do you know? Jess,” He sighs, turning his head to look around. “I don’t want to be that guy that gets treated like crap, then will turn around and forgive you after every apology. I have more self respect than that.”

 

Jess grabs his hand, looking him in the eye. “I  _ promise _ I will never speak to you or treat you like that  _ ever _ again.”

 

“You promise?”

 

“Cross my heart, and all that. Or we can do a blood oath, or even a pinky swear. Whatever it takes for you to give me a second chance, tell me and consider it done.”

 

Oliver stands there thinking, Jess’ heart going a mile a minute as he waits for his response. “Is that offer for me to shove you in the lake still open?” He finally asks.

 

“As soon as the ice thaws, I’m all yours.” 

 

Oliver squeezes his hand, face softening as he nods. “Okay, one more chance. Please don’t make me regret it.”

 

“You won’t, I swear.” In a swift movement, Oliver gives him a quick kiss. Usually if they’re in Hartford, especially at or near Chilton, he’s not too into the PTA. Before Jess had thought he was just shy around all the Chilton kids, but he soon figured out that it’s because if someone sees him and recognizes him, it would most likely get back to his parents.

 

Oliver pulls back slowly. “Bye, Jess.”

 

Jess grins. “Bye.” He leans back on his car as he watches Oliver leave, glad things are finally returning to normal. Getting in his car, he turns over the engine, grin still firmly in place.

 

“I’m assuming you smoothed things over.” Rory teases him.

 

“Yup.”

 

She snorts, cracking her book open. “You are such a dork.”

 

“Takes one to know one.” He fires back.

 

“What are you, ten? That’s the best you can come up with?”

 

“I can also do this.” In a flash, he snatches her book off her lap and shoves it in his door compartment where she can’t reach.

 

“No problem.” He glances over to see her reach into her bag and pull out another book.

 

He shakes his head. “Nerd.”

 

“Dork.”

 

0000000000000000000000000000 

 

Winter break is more painful than he thought it would be. All day, he’s stuck in the diner. At least during school he had an excuse to go some place. The only time he can leave now is with Luke, who is literally the slowest shopper in the world, or with Lorelai to go to the Inn, but since Rory is out of school too, she gets first dibs on jobs, leaving nothing for him. The worst part is, since school is out, that means no more books, or book, for him. He tried reading his chemistry textbook, but that was worse than the boredom.

 

Nobody is even here to talk to him and keep him company, since Luke didn’t go as far as banning anyone from coming to see him downstairs in the diner. Dean and Oliver are both out of town with family for the holidays, Rory and Lorelai are having a movie marathon at the crap shack, and Lane is spending time with her dad trying to find items for the store. The only people here are the usual town loonies and of course Luke.

 

Just so he doesn’t go completely insane, Jess takes one of the salt shakers and starts to push it back and forth on the counter between his hands. This goes on for fifteen minutes before Luke stomps over and snatches the salt shaker up mid slide.

 

“Enough. You’re driving everyone insane.” He hisses at him.

 

“But there’s nothing-”

 

“ _ Do not _ even finish that sentence.” Luke cuts him off. “If you’re so bored, then go clear some tables.”

 

Rolling his eyes, he gets the bin from behind the counter and starts to collect the dirty dishes. The whole time he’s doing this, he gets great amusement from watching Taylor grumble incoherently as he tries to do the crossword puzzle of today from the  _ Stars Hollow Gazette. _ Jess shakes his head, all the crosswords in that thing are so easy, he could do them in his sleep.

 

Figuring he could get some entertainment  _ and _ be able to annoy Taylor, he innocently walks behind him as he grabs a plate, glancing down at the paper.

 

“Boats.”

 

“Excuse me?” Taylor glares at him over his shoulder.

 

“Five letters, seven down, sites for busy hands. The answer is boats.”

 

Taylor scoffs. “Yes, I’m sure…” He glances down and realizes it fits. “You, uh, must have just gotten lucky.”

 

“Really? Try me.”

 

“Fine.” Taylor sits up, clearing his throat as he scans the crosswords. “How about, four letters, exclude.”

 

“Omit.” Jess doesn’t hesitate to answer, amused when Taylor huffs. “What? Think I just got lucky twice? Because if that’s the case I should go buy a lottery ticket.”

 

“Six letters, operatives.”

 

“Agents. This is really bothering you that I’m getting these, isn’t it?” By now, most of the people in the diner are watching them, including Luke who looks torn between enjoying this and putting an end to it.

 

Taylor smirks as he finds the next one. “Ten letters, antibiotics from blue mold. Let’s see you get this one.”

 

It takes him a second longer, which makes Taylor’s smirk grow even more if that’s possible. “Penicillin.” His smirks drops.

 

“You’re cheating. I don’t know how, but you are.”

 

Jess chuckles. “Okay, Taylor, whatever you say.”

 

For the next week it becomes a daily routine for Taylor to come in and start quizzing Jess on different crossword puzzles out of some book, hoping to stump him or to figure out how he’s ‘cheating’. Luke lets it happen, since as Jess pointed out to him one night, it’s not breaking any of the rules he made. They have a crowd that watches them every morning now too, waiting to see if Jess ever gets stumped, which he doesn’t.

 

“Conservative Roman senator, four letters.”

 

“Cato.” Jess answers from the counter, head pillowed on his arms. Luke can tell he’s already bored of this little game, but if the kid tries to quit, Taylor would just assume that Jess doesn’t know the answer and count it as a win. Jess, being the stubborn brat he is, refuses to lose, so here they are, going back and forth every morning until one of them gives up. 

 

“Colds that last a long time, seven letters.”

 

“Ice ages.” Jess sighs as he sits up, propping his head up with his hand. “C’mon, you could at least make this a little more difficult.”

 

Taylor huffs as usual next to him at the counter, flipping through his little book this time. “How about… they come in last, three letters.”

 

“XYZ.” He stands up. “Luke, bathroom.”

 

Luke nods that he heard, watching Jess head to the back.

 

“He has to be cheating, I just know it.” Taylor grumbles like clockwork, flipping through his book.

 

“You know, has it ever occured to you, Taylor, that Jess really is just that smart?” Luke asks as he takes the man’s empty mug.

 

Taylor scoffs as he shakes his head. “That hooligan? No, the only way he knows all the answers is if he’s cheating, I just don’t know how he does it yet. But let me tell you, when I do, will his face be red.”

 

Luke feels a surge of protectiveness over Jess, and anger at Taylor for just underestimating his kid like he always does. “That ‘hooligan’ could think circles around you. Hell, he’s smarter than just about everyone in this crackpot town. He reads more than anyone I know, and yes, that includes Rory. In fact, I’ve seen him  _ help _ her on her homework from the fancy prep school of hers multiple times, meaning he doesn’t just  _ know _ the stuff, but understands it well enough to teach it to someone else. So you’re going to quit this little hunt to embarrass him and admit that, yes, he really does know all the answers. Capisce?”

 

Taylor stares at him wide eyed, frozen in place. Is it possible that for the first time he made the great Taylor Doose speechless?

 

Jess comes back from the bathroom, oblivious to everything that happened. “Alright, time for round two?” He asks as he plops down on the stool.

 

Luke glances at Taylor, making the man fidget. “Yes, well, um, I think you’ve certainly proven that you have a, uh, broad knowledge of many things. Would you look at the time? I really must be getting back to the market.” Quickly paying his tab, he scampers out and down the street.

 

“Huh.” Jess comments as he watches Taylor leave. “You have any idea what that was all about?”

 

Luke shrugs as he puts the money in the till. “Beats me. Just Taylor being Taylor.”

 

“Right.” Luke can feel the holes from Jess staring at him. “Just Taylor being Taylor.” He repeats, staring a little longer before getting up and helping out without being asked.

 

0000000000000000000000000000

 

Jess wakes up energized. Getting ready in record time, he saunters down to the diner.

 

“Guess what day it is!”

 

“Saturday.” Rory answers from the counter.

 

“Elvis Presley’s birthday.” Lorelai answers just as quickly as Rory did.

 

Rory turns to her mom. “Really?”

 

“Yup, along with David Bowie and Stephen Hawking.”

 

“Huh, I did not know that.” Jess admits. “How did  _ you _ know that?”

 

“For Christmas, Babette got me one of those calendars that shows celebrity birthdays for that day.”

 

“Well, as interesting as that is, it’s not what I was going for.”

 

“Is it the day I invest in ear plugs?” Luke mumbles as he makes a new pot of coffee.

 

“It is January 8th, meaning this is my first day of freedom.” Jess ignores Luke. “I am no longer confined to this place, I can come and go as I please.”

 

“ _ After _ you finish your shift.” Luke cuts in. 

 

“Fine, I’m free  _ after _ I finish my shift.” He corrects. “Happy?”

 

“Ecstatic.” Luke answers in a deadpan tone.

 

Jess shakes his head and rolls his eyes. “So,” He leans on the counter to talk to Rory. “What are your plans for the weekend?”

 

“Shopping.”

 

“Yeah, but not the fun kind.” Lorelai interrupts with her mouth full.

 

“There’s a fun kind of shopping?” Luke asks before Jess has the chance to.

 

It’s Lorelai’s turn to roll her eyes. “My dad’s sixtieth birthday is coming up, and I have no idea what to get him. And that reminds me, Jess, how’s your Wednesday night looking-”

 

“No.”

 

“But you don’t even know what I’m about to ask.”

 

“Does it involve me stuck going to this thing too?”

 

“Maybe.” She says reluctantly.

 

“Then no. I’m still mad about the Yale ambush.” 

 

“Jess, c’mon, you owe me. I drove out to New York to get you, and I just had my mom on the phone saying my dad is insisting  _ you _ go so he can apologize, and you owe me!”

 

“Luke!” Jess whines, hoping he can get him out of this.

 

Luke shrugs as he wipes down a mug. “He did get you to fill out all the college applications, I say you go.”

 

“Whoa, wait a minute, college applications? What college applications?” Lorelai and Rory both look excited at the news.

 

Great, he filled out all those stupid things upstairs for the sole reason that no one would find out. He’d never admit it, not even to Luke, but something Lorelai had said when she was driving him home from New York really struck a chord with him. She didn’t mean it, but when she said he doesn’t care about his future, it made him realize that he does. He does care. He doesn’t want the sad life that Liz leads and wants to do something with his life. 

 

“I was bored. Just because I filled them out doesn’t mean I’ll get in  _ or _ that I’ll go if I do.” He uses the same lie with her that he used weeks earlier with Luke. “It was either fill those out or get in another crossword fight with Taylor.”

 

“He’s going.” Luke says more firmly this time.

 

0000000000000000000000000000

 

Later in the day, Jess and Rory headed into Hartford to scour thrift shops in search of a gift for Richard. They figured it’s the best place to find something he would like, and has the added bonus of being easier on their wallets.

 

“So, I saw Dean this morning.” Rory says casually as she flips through the vinyl records. 

 

Jess pauses in his search through the bookcases and turns to her with a shocked expression. “Really? How’d that go?” He knows the two haven’t seen each other since the break up, something that’s just short of a miracle considering the size of the town.

 

“I think it went well. He was bringing over a box of some of my things I had let him borrow. Books, music, that sort of thing.” She finally looks up from the records. “We decided we can still be friends.”

 

He stuffs his hands in his pockets, completely giving up on his search. “Ror, are you sure this is a good idea?”

 

She shrugs, going back to flipping through the records so she can avoid his gaze. “Why not? You and him are friends.”

 

He does a half chuckle. “Well, yeah, but we weren’t dating for the last two years.”

 

“So? It just means we can be friends without all the pressure of dating. Trust me, it’ll be fine. He even asked me to get some coffee with him soon, as friends of course.”

 

“He’s dating again.” Jess blurts out.

 

Rory stops, but doesn’t look at him. “What?” She asks, voice a little too even.

 

Damn it, him and Lane were going to sit her down and gently tell her, not blurt it out in the middle of birthday gift shopping for her grandpa. “Yeah, it’s new though. As in just a few days ago new.”

 

“Who is it?” Rory goes back to flipping through the records again.

 

“Lindsay Lister.”

  
  


“Oh, well, Lindsay is nice. I was in the fourth grade with her. This one time, we took a field trip to Mark Twain’s house and I really wanted to get a magnet in the shape of his head, but I didn’t have a quarter so she let me borrow a quarter, and then the next day when I tried to pay her back, she said it was fine.”

 

“Wow, guess we’re looking at the next Mother Teresa here.” He says sarcastically.

 

“What? You don’t like her?”

 

“Let’s just say she’s not at the top of the list for the next Nobel.”

 

Rory slaps him on the arm for that. “Jess, don’t be mean. Lindsay is a very nice person, I’m glad Dean moved on to someone nice.”

 

“That’s the third time you’ve described her as ‘nice’, and I wouldn’t be so sure about that. She’s been scoping him out from day one and scooped in to take him the second you two broke up. Hell, she’s been in that stupid home ec class with Lane and I since September, and she still doesn’t remember our names.”

 

“Well, you two keep to yourselves a lot, especially in that class, maybe she just doesn’t know you two that well.”

 

“Rory, I’m the  _ only _ guy in that class, she totally knows who I am. When Dean brought her to our table at lunch, she said to me and I quote, ‘You’re, like, that gay kid in my home ec class right?’.” He says in his best valley girl impression.

 

“Oh, well, maybe she was just nervous. You do tend to send out ‘back off’ vibes with people you don’t know.”

 

“Yeah, maybe.” Jess focuses his attention back to the bookcases, still not convinced. His gut has never let him down before about a person, and he’s seriously getting bad vibes from her.

 

“Hey, look what I found! It’s perfect!”

 

Jess glances over, reading the title. “Chuck Berry Live at the Fillmore. Not bad.”

 

“And it’s only fifty cents!”

 

“Hey, if I pay for the thing, will you start worshiping me? Because if Lindsay is a saint for lending you a quarter, then according to your logic that should make me a god if I give you two.”

 

“And here I was, about to help you look now that I’m done. Too bad.” She sticks her tongue out, leaving him alone.

 

000000000000000000000000000 

 

In the end, Jess ended up getting Richard  _ The First Men in the Moon _ by H.G. Wells, a book he remembers the man talking about one of the times he was over for dinner, and annotated it as an added touch. When Jess first arrived with the other two Gilmores, things had been pretty awkward, but Richard pulled him aside and apologized for his behavior back in November. He explained his thought process again, mentioning Lorelai’s past as one of his biggest regrets, but then went on to say that despite not going to a big university, Lorelai still has a great life and is sure that whatever Jess chooses to do, he will too.

 

With the air cleared, the two head back into the sitting room, where the presents are all neatly stacked on the coffee table. Emily hands him and Richard their drinks, and Richard sits down next to his wife while Jess sits next to Lorelai on the couch across from them since Rory has already taken a seat on the floor by her grandpa’s feet.

 

Lorelai wraps an arm around him after he sits, giving him a little squeeze. “You okay?” She whispers while the other three are busy talking with each other.

 

He gives her a reassuring smile, surprised he doesn’t have to fake it. “Yup.”

 

“Good.” She drops her arm, watching Richard open his presents.

 

He opened Jess’ first, excited and already flipping through the book before Emily has him put it down so he could get through the rest of his presents. Next is Lorelai’s, which she ended up getting him the complete history of the Peloponnesian war, with the added bonus of the bowtie she was originally just getting him wrapped around it. Emily gets him a cigar humidor and Rory the Chuck Berry vinyl. 

 

As he finishes up giving everything a once over again, Rory gets up and goes over to sit on the chair next to Lorelai.

 

“So you had a good birthday, Grandpa?” Rory asks.

 

“I have to say, this is the most wonderful birthday to date.”

 

The doorbell rings, Jess still not used to the fact that no one moves to get it since the maid will answer it. God, Luke would hate it here.

 

“Would you like some more champagne?” Emily asks.

 

“Oh, why not.” Richard laughs, setting his glasses on the coffee table.

 

“-ne of the porch lights is burnt out.” An older woman’s voice says from the doorway, causing Emily to freeze like she’s seen a ghost. “Perhaps the simple act of glancing outside a window once in a while might have alerted someone to the situation.” Everyone starts to glance at each other, so clearly Jess is the only one not in the know.

 

“Gran?” Lorelai asks, probably for his benefit.

 

“Trix, is that you?” Richard calls out. “I’ll be. What a surprise.” He gets up, heading for the door.

 

“Mom, did you know Grandma was coming?” Lorelai asks a still frozen Emily. Jess has never seen her like this. She’s always so put together, he didn’t even think she was capable of being surprised.

 

“Oh my god.” She utters.

 

“Okay, no seems like a safe answer.” She turns to Jess, filling him in. “Gran is my dad’s mom.”

 

He nods. “Yeah, I gathered as much.”

 

“Emily, come here! Come say hello to this delightful creature that just walked in!”

 

Emily finally seems to snap out of it, moving like the wind. “Oh my god!”

 

“C’mon, let’s go see if she makes a break for it.” Lorelai grins, her and Rory jumping out of their seats. 

 

Jess follows at a slower pace, feeling out of place during this little reunion. Maybe  _ he _ should make a break for it. He hangs back as everyone greets this old lady who looks to be in her eighties. She has a posh accent, more so than Emily’s, and dresses like she just walked out of a Dickens novel. He does get a little joy out of seeing Emily get knocked down a peg or two by this woman, remembering how Emily had treated him the first time he was here and thinking this is karma at its finest.

 

His attitude changes though when they head back into the sitting room, where he’s still hovering unsure of himself.

 

She stops, staring him down. “And who is this young man, loitering in the drawing room? Chop chop, I haven’t got much time left on this Earth if you couldn’t tell.”

 

“Oh, um, Jess. Ma’am.” He tacks on at the end, feeling, and probably looking, like a deer caught in the headlights.

 

Lorelai comes to his side, looping an arm through his. “Gran, this is Rory’s best friend, Jess Mariano. He’s the nephew of a good friend of mine. Jess, this is my dad’s mother.” 

 

“Hello, ma’am.” He holds out his hand to shake.

 

She stares at his hand until he takes it back. “Rory, dear, I’m tired from all the travel. Can you possibly lead me to a place to sit?” She ignores him in favor of Rory.

 

“Of course, Gran.” 

 

She sits with a sigh, Jess trying his hardest to blend in with the wallpaper as Lorelai leaves his side to go back over to her mother.

 

“Oh, Emily, you’re still here.”

 

“Yes, of course. Can I get you some champagne?”

 

“If you would like me to be violently ill tomorrow.” She scoffs.

 

Lorelai leans in to whisper something, but Jess can’t hear from his side of the room.

 

“Here, I’ve got you covered, Trix.” Richard hands her something, which she thanks him and sips.

 

Jess sits at the end of the couch with Rory between him and Lorelai, while Richard and Emily sit across from them. They fall into small talk, which Jess spends the whole time silent. He perks up when Richard’s mom mentions that she had rented out her house to Korn, amazed he hadn’t known about this before. She also mentions a dinner tomorrow, pointedly saying a  _ family _ dinner, at the Inn to see where Lorelai works.

 

Rory glances at him and Lorelai, worried since the three of them and Oliver were all planning on going to the Stars Hollow High Winter Carnival together.

 

“What?” Trix, or Gran he’s not sure what to call her, notices Rory and Lorelai’s shifting.

 

“It’s just, the three of us were already planning on going to the winter carnival at the high school along with Jess’-”

 

“Friend.” Jess fills in, worried Lorelai might say boyfriend. Normally he wouldn’t care if she told someone, but that thing Oliver had said stuck with him. ‘Old money, old values’ indeed.

 

“Right,” She gives him a weird look. “His friend.”

 

“But we can skip it.” Rory cuts in.

 

“Absolutely not. Rory,” There she goes, excluding him again. “You are a young person who works hard. It’s equally important to have fun. You go to the carnival with your friends.”

 

Rory grins. “Thank you.”

 

“Lorelai, you’ve had enough fun in your life.”

 

“And then some.” She adds as a joke.

 

“Then it’s decided. Dinner will be for the grown-ups.”

 

Jess partially zones out as Richard talks about his birthday with his mom, doing a good job of hiding his amusement when she not-so-subtly cuts down Emily’s gift. 

 

“Well, I’m quite weary from my travels. Richard, would you show me to the guest room so I may freshen up?”

 

“Right this way, Trix.” Richard stands, ready to lead her upstairs.

 

“Emily, this should take about twenty minutes, giving you ample time to pull my gifts out of storage and have them placed about the room as if they actually stand there all year.”

 

“Yes, Mom.”

 

“And make sure you inform your kitchen staff that I desire dinner promptly in exactly thirty minutes. Do you think you can handle that?”

 

“Right, Mom. Of course.”

 

Gran nods, leaving the room with Richard. Emily slouches, tossing Gran’s gloves to the side that had been stuffed in her hands as soon as the woman arrived.

 

“Need help with those gifts?” Lorelai offers.

 

“Yes, please.”

 

Unsure where to go, Jess follows after them to the basement. He never thought he’d see the day where he’d actually  _ prefer _ to be in Emily’s company. Hell, he’d take Mrs. Kim over this old lady any day.

 

0000000000000000000000000

 

Dinner is a tense affair. Richard let his mother sit at the head of the table, him sitting across from Jess and Rory next to Lorelai. Jess, wishing once again that he could be invisible, swapped places with Rory so he doesn’t have to sit next to the woman.

 

“So, Gran, how’s London been?” Lorelai asks to break the silence.

 

“The weather is just dreadful as usual, wreaking havoc on my joints. I’m not sure how many more years of traveling I have left in me, and would much rather spend the miniscule amount of time I have with my son.”

 

Richard shakes his head. “Oh, Trix, quit with that silly talk. You’ll outlive us all, just you wait and see.”

 

“The wicked always do.” Emily quietly mumbles into her drink, Jess the only one to hear her. Trying hard not to laugh, he coughs into his napkin, which has the unfortunate side effect of having the old lady’s attention focus on him.

 

“Now, you said your name is Jess, correct?”

 

Jess nods, swallowing. “Yes, um, Mrs. Gilmore.”

 

“Please, call me Gran, everyone else does. Things can get confusing considering there are two other Lorelais in the room.”

 

“Trix, this is the young man I told you about over the phone.” Richard cuts in, getting giddy like he had when he had been introducing him and Rory to his Yale buddies.

 

“Ah, yes, I remember. Tell me, what are your plans for after high school? I am assuming you applied to schools?”

 

Richard shifts, no doubt ready to jump in with a subject change when Jess surprises him. “Yes, I have.” Lorelai smiles across from him, encouraging him to keep going. 

 

“Really?” She looks shocked. “Which ones? Local? Trade schools perhaps?”

 

Okay, now she’s just getting on his nerves. “Harvard, Yale, Princeton.” He lists off unflinching.

 

“Hm, all of those schools are, how do I say,  _ exclusive.  _ If by some miracle you did get in, how are your parents planning on affording it?” Jess clenches the napkin in his lap. He can’t stand the way she’s speaking to him now, like she’s just humoring him.

 

“I don’t know about my parents, but my uncle and I will figure it out,  _ when _ I get in. Excuse me, I need to use the restroom.”

 

Standing, Jess gets out of there before he leaps over the table and decks the woman. Fleeing to the kitchen, he leans over the sink to open the window and lights a cigarette as fast as he can, closing his eyes as he feels the nicotine do its job at calming his nerves. One of the joys of being eighteen, he can legally buy his own packs now. No more overpaying some guy to go buy them for him. Making sure to blow all the smoke out the window, he sits up on the counter sideways, one leg folded under him and the other hanging off the counter completely. One of the kitchen staff walks by, giving him a strange look.

 

“What’re you staring at? Never seen a guy smoke before?” He snaps, making her flee. Great, now she probably thinks he’s one of those asshole rich kids.  _ That _ couldn’t be farther than the truth.

 

“And here I thought I was the only one that talked to the staff that way.”

 

“Shit!” Jess jumps, nearly dropping his cigarette in the sink. He must be  _ really _ out of it if he didn’t notice Emily come in.

 

“Hand that here.” She demands, holding her hand out.

 

Figuring he’s busted, he hands it over, jumping down from the counter. “So-” He starts to apologize before she cuts him off.

 

“God, I can’t  _ stand _ that woman!” She complains, surprising him by taking a long drag of his cigarette without so much as a wince. She tries to hand it back to him, but he shakes his head, pulling out a new one and lighting it. “Every time she comes back here, she leads me to shamefully hide these things so I don’t go completely insane.”

 

Jess leans back against the counter. “My uncle wants me to quit, and I’ve been pretty good about it lately, over a month without one, but I figured Luke would understand making an exception this once since throwing down with a great-grandmother tends to be more frowned upon than smoking in most social circles.”

 

“And she’d win too.” Emily jokes, causing Jess to chuckle. Now he’s starting to see where Lorelai got her humor from.

 

“Well, with all her  _ exclusive _ schooling, who could blame her? I’m just the lowly peasant boy, bein’ taught by me uncle.” He drops his voice into a southern drawl.

 

She smirks. “How is Luke? Is his diner doing well?” She asks, growing more serious.

 

“Yeah, Luke’s Luke. He’s like the pink energizer bunny, just keeps going steady.” Jess takes his cigarette and taps it out the window, watching the ashes fall. “He, um, adopted me actually.” He doesn’t know why he’s telling her about this, he hasn’t even told Dean and Lane yet.

 

“I’m not surprised. From what Lorelai has told me, he’s very fond of you.”

 

Jess shrugs. “He’s not bad. Better than my birth parents, but the bar was pretty low to start with, so that’s not saying much.”

 

They stand in a comfortable silence with their cigarettes, vaguely able to hear Richard laughing about something. “It’s hard, being an outsider in your own family, wouldn’t you agree?” Emily speaks up. “No matter how hard we try, we’ll never measure up to that woman’s standards, solely because we aren’t pure-blooded Gilmores.”

 

“Two against four, I’d say our club is a little more  _ exclusive _ than hers.”

 

A grin slowly forms on her face. “I suppose it does, doesn’t it.” Stubbing out her cigarette on one of the dirty pans in the sink, she heads over to one of the cabinets, pulling down a bottle of some amber looking liquid. She pours a little into two glasses, coming back over and handing one to him. “I say this calls for a toast. To the outsiders.” She holds up her glass.

 

Ah, what the hell? “To the outsiders.” He cheers with her, watching in fascination as she downs her glass in one go. Who would’ve thought Emily Gilmore could be a party girl?

 

He sips his drink, savoring the taste. The one glass is probably worth more than what he makes in a month, at Luke’s and the Inn combined. “So, are things serious between you and this  _ friend _ you’re going to the winter carnival with?”

 

Jess chokes on his drink, coughing as his throat burns. “I don’t-”

 

Emily rolls her eyes, pouring herself another glass. She offers him more, but he shakes his head. “Please, I’m not dense. The way you jumped in to correct Lorelai, one would think the room was on fire. Now, what’s his name?”

 

“Him? What makes you think-” She stares at him with her patent ‘Do you really think I was born yesterday’ look. Jess focuses his attention on his empty glass, running a finger back and forth on the rim. “Oliver Stone. He was the one I was talking to at Rory’s student government speech. Please don’t mention anything though, his parents don’t know and he really doesn’t want them finding out from someone else.”

 

She nods. “Very well.”

 

“You really don’t care?”

 

Emily scoffs. “Honestly, I may be old, but I’m not archaic. Oliver is a wonderful boy, I’ve know him since he was young. I’m in the D.A.R. with his grandmother.”

 

“Huh.” Jess isn’t surprised, from what he’s heard, everyone knows everyone in the Hartford upper class. “You got any pull for some embarrassing photos? I need some payback for all the ones Luke likes to show off.”

 

She shares a grin with him. “I’m sure I can arrange something.”

 

Lorelai chooses now to burst in, blinking at the scene in front of her. “Did I miss something? I don’t smell burning toast, so I can cross a stroke off the list.”

 

“Lorelai, what are you doing here?”

 

“What am I- Mom, what’s with the Blues Brothers moment here? And I’ll be taking this,” Lorelai snatches Jess’ cigarette from his hand, stuffing it out and shutting the window. “Alright, you had your fun, go back to dinner, kid. And your plate better be as clean as a whistle when I get back or no dessert.”

 

“But-”

 

“Go. Before I decide to change my mind and tell Luke all about your activities tonight.” Rolling his eyes, he pushes off the counter, ready to go back out to the firing squad. Lorelai stops him again, holding out her hand. With a sigh, he reaches into his pocket and slaps the pack in her waiting hand. “Thank you. I’ll be right out, babe, I just need to talk to Carrie Fisher here for a minute.”

 

Lorelai stuffs the pack into her purse, waiting for Jess to leave the room completely. “Seriously, Mom? What the hell?” She hisses when the coast it clear. Grabbing the cup Jess had left behind, she sniffs it, nearly knocking her off her feet. “Whiskey too?! He’s eighteen! He doesn’t need to be drinking and smoking.”

 

“Quit being so hysterical, Lorelai, one little cup isn’t going to kill him.” Emily brushes her off, putting the two cups in the sink.

 

Feeling the rage that she usually associates with her mother, Lorelai just snaps. “Yes, it can! His mother is an alcoholic, Luke’s checked and that sort of thing is hereditary! And Luke and I are really trying to get him to quit smoking because his grandfather died of  _ lung cancer, _ from you guessed it,  _ smoking! _ So Mother, please, for once in your life, do me this one favor and just butt out!”

 

For once her mother is speechless. For all the times Lorelai wishes she had a camera, this is it, because she has never made the all powerful Emily Gilmore speechless before.

 

Her mom shocks her a second time in as many minutes by bowing her head and apologizing. “I’m sorry, Lorelai, I had no idea. Had I known I never would have urged him to have a drink with me.”

 

Lorelai sighs, rubbing her forehead. “No, Mom, of course you wouldn’t have known. Jess isn’t exactly known for his chattiness.”

 

“Still, it’s as you said, he is eighteen, so I apologize for overstepping.”

 

Lorelai shifts, not used to her mom being this cooperative. Having Gran around really does affect her. “It’s fine.” She lets it go. “What were you two bonding over anyway? The best ways to kill Gran and get away with it?” Unlike her dad, she’s noticed how hard Gran has always come down on her mom, and now Jess it seems.

 

“We have formed a club.” Emily informs her with glee.

 

“Really?” Lorelai asks, glad the two are starting to get along. Now she knows how Luke felt when she and Jess used to fight and finally started connecting. “And how does one go about to join this little club of yours?”

 

“I’d hate to inform you, but you just don’t qualify. We should be heading back out now.” She leads the way, pausing before exiting the kitchen. “Oh, by the way, I’d love to formally meet that boyfriend of his some time. It’s only fair, since we put Rory through the same thing.” With that, she leaves Lorelai standing speechless in the kitchen. Jess and Emily  _ both _ seem to be full of surprises this evening.

 

00000000000000000000000

 

Jess and Oliver sit waiting in the diner where they plan to meet Rory so the three of them can head over to the carnival. After the  _ delightful _ dinner with Gran, Rory was worried he would have changed his mind on letting her tag along. Before her mom was going to be there as well, making her less of a third wheel, but Jess assured her that it’s fine. It’s a school carnival, not a five star restaurant, this is supposed to be a group thing anyway. If Lane wasn’t working at the marching band’s booth, she would have joined them as well.

 

Jess is the one that  _ doesn’t _ want to go, but Oliver really wanted to and with the whole fight they had last month, Jess figured he’s on thin ice as it is and doesn’t want to disappoint him again. 

 

They see Rory heading their way and get up to meet her outside. 

 

“Are you sure you guys want to go to this thing?” Jess asks as a greeting.

 

Rory rolls her eyes, while Oliver loops his arm through his to start leading him to the town square where the carnival is being held. “Oh, boy.” Rory mutters, walking on his other side. If he didn’t know any better, he’d think they planned ahead. Now he understands how cows feel when they’re being corralled. Poor cows.

 

“I’m just saying, there are plenty of other, more interesting things to do on a Thursday night. Staring at paint dry or watching the grass grow, just to name a few.”

 

“You need more social interaction than just the same four people.” Oliver points out. “Plus, this thing is raising money for  _ your _ school, don’t you want to support it?”

 

“Hey, it’s not my school by choice. And I already socialize with these people every day, they’re all annoying idiots.” Jess scoffs.

 

“Just a tip, but maybe they would be less annoying if you stopped calling them idiots.” Rory points out.

 

“I’ll stop calling them idiots when they stop being so annoying.”

 

Rory sighs. “All that’s missing is the trench coat and then you’d have your unabomber existence complete.”

 

Jess has a great reply about Santa bringing one for him next year when he gets interrupted by a shrill voice. “Rory!”

 

The blonde little munchkin runs past him and Oliver, making them stop abruptly so they don’t trip over her, as she tackles Rory in a hug. “Clara, hi!”

 

Oliver watches in amusement as Jess tries to hide behind him, but it’s too late. “Jess!”

 

“Munchkin.” He greets her reluctantly. “Oliver, this chatterbox is Clara, Dean’s little devil- I mean sister.” Oliver gives her a wave, but doesn’t get the chance to speak.

 

“Jess, is he your  _ boyfriend?” _ She grins at him.

 

Luckily, Jess gets saved by Dean running up. “Clara, I told you to stay with me. You can’t just run off.” Maybe Jess spoke too soon, because when he looks up he sees Lindsay standing there too, looking more annoyed than him if that’s possible. The annoyed expression turns to a smile when Dean glances over at her.

 

“Rory, Jess, are you guys going to the carnival too?” Clara asks. If she were a dog, her tail would be wagging.

 

“Um, yup.” Rory answers.

 

“We should all go together then!” Clara proposes, ignorant to all the tension. “Please, Dean? I haven’t seen Rory in forever!” She turns to her brother, giving him the old puppy dog eyes.

 

Dean winces. “I don’t know, Clara…”

 

Lindsay wraps an arm around Dean’s waist. “I think that sounds like a great idea.”

 

“See, Dean! Lindsay says we should!”

 

“Well, I guess if it’s okay with the others.” Dean glances at the rest of them.

 

“Why not?” Rory forces a smile.

 

“Yay! To the carnival!” Clara cheers, running ahead. While Dean and Lindsay are distracted by trying to stay with her, Jess shoots Rory a look to see if she really is okay. She nods, sending him a more sincere smile.

 

“To the carnival…” Jess says with a sigh. Oliver takes his hand, squeezing it reassuringly as they cross the street.

 

0000000000000000000000000

 

Lindsay spends the whole time clinging to Dean like she’s staking her claim. It’s nauseating. And poor Rory is stuck with Clara as she sticks to her side the whole time with her never ending questions.

 

“So that’s Lindsay?” Oliver whispers to him as they keep a few paces behind the group.

 

Jess groans. “Yup.”

 

“And Dean and Rory really are just friends now?”

 

“That’s what they told me.”

 

“Wow. It’s just so weird. I mean, it’s always been Dean and Rory. They’re like Ross and Rachel, it’s so weird seeing them split up and Dean with someone else.”

 

“At least you don’t need to eat lunch with the two of them everyday. I swear, I feel myself getting more stupid with every word she says.”

 

Oliver nudges him. “You’re exaggerating. Plus, you are a little biased. In your mind, no girl can be better than Rory.”

 

Jess drops the conversation as Clara turns around and runs over to his side. “Jess! Quit being a slowpoke and come on!” She grabs his free hand, tugging him along.

 

“Yeah, yeah, I’m comin’, runt.”

 

“So, you’re Oliver?” She asks.

 

“Um, yup.” Oliver smiles politely.

 

“Does he really wash his hair? Because he always tells me he does, but it sticks up all crazy like and mine doesn’t do that when it’s clean, only when it’s dirty.”

 

“I’ve told you a thousand times, I wash my hair!” Jess cuts in.

 

“Are you sure?”

 

“Yes.”

 

“Are you sure?”

 

“Yes.”

 

“Are you sure?”

 

“Dean, come collect your thing!” Jess calls out.

 

“Hey, Clara, why don’t we go get some snow cones?” Dean yells out for her, sending Jess an apologetic look. “You guys want any?” He asks. Both Lindsay and Rory nod, while Jess and Oliver decline the offer.

 

With the attention span like a goldfish, Clara goes running back over to Dean, trying to decide if she wants a cherry flavored one, or a blue raspberry one. Dean leads her away, leaving Lindsay with the three of them.

 

“So, Lindsay, how have you been?” Rory asks to get the conversation started.

 

“Good.” Is all she answers. “You used to go to our school right? I think I remember seeing you before.”

 

Rory crosses her arms, nodding. “Yup. We were actually in the same fourth grade class. We went on the field trip to Mark Twain’s house and you gave me a quarter so I could get a magnet.”

 

“Really? Sorry, I don’t remember.” She doesn’t look sorry, the little- Oliver nudges him subtly in the side, shooting him a look that clearly reads for him to be nice. He mouths that he is.

 

Rory, ignoring the whole exchange, waves Lindsay off. “No, of course, it was a long time ago.”

 

They lapse into another silence, this time broken by Lindsay. “You, uh, go to that private school now, right? The one in Hartford?”

 

“Yup. Oliver does too actually. Jess and Oliver met at a school thing. I’m in student government and Jess came to see my speech and Oliver was sitting behind him. We’re on the school paper too, but we hadn’t really talked much before, but now we do, since him and Jess are dating now. Wow, I’m talking a lot, sorry. It’s like, since Clara’s gone I’m filling up a vacuum. Hey, is that Lane? I’m going to go say hi. I’ll be right back.”

 

Rory makes her escape, leaving Jess and Oliver alone with Lindsay, the little traitor. Jess is going to kill her later for this.

 

“How long have you guys been dating?” Lindsay asks so the conversation won’t lag again.

 

“Since the beginning of November.” Oliver answers for them. God, Jess is grateful that he knows when social interactions make Jess uncomfortable, like right now.

 

“Cool. Rory’s your sister, right?” She asks Jess directly. 

 

Jess nods, sticking to one word answers like he usually does at lunch with her. “Yup.” There’s no point in clarifying things for her, if Dean is smart he won’t stick around with her long enough for it to matter.

 

“Cool.” She nods again, getting the hint that he doesn’t want to talk. They fall into an uneasy silence, one that not even Oliver can break.

 

000000000000000000000

 

Dean and Clara come back with a snow cone in each hand, cherry since that’s all they had. Sensing the tension, Dean suggests him, Clara, and Lindsay go try some ice bowling. Handing over a dollar to a guy running one of the carnival game booths, Jess starts chucking the balls at the stacked bottles, missing every time. It doesn’t matter since he’s not trying to hit the bottles, although that would be a bonus, he mostly just wants the chance to throw something at high speed.

 

After he’s done, he steps aside to give Rory a turn, holding her snow cone for her. “Imagining that was Lindsay’s face?” Oliver asks, taking his free hand.

 

“How could you guess?”

 

“Don’t tell anyone this, but I’m psychic.” He grins, causing him to grin slightly too. “Ah, so he can smile! Relax, the night’s almost over. When we’re done, we can go watch a movie, your choice.”

 

“Promise?”

 

“Even your favorite stupid E.T. ripoff. Plus, I’m pretty sure I saw snow in the forecast, so I’ll stay the night too.” Jess smiles, feeling marginally better.

 

They both look up at the sound of bottles crashing and Rory jumping up and down. “I did it!”

 

The guy running the booth hands her the stuffed teddy bear, congratulating her. Oliver pulls out his own wallet, hanging over a dollar. “The thing is rigged, I’m telling you.” Jess comments as he hands Rory back her snow cone. 

 

Without a word, Oliver lines up the shot and nails it on his first try. “You’re looking at the Hartford little league pitching MPV three years in a row.” He brags after thanking the guy for the bear. “You just suck at throwing things.”

 

They start walking around again, Rory heading off to talk to one of her old teachers working at a booth. Jess never had the guy, so him and Oliver hang back. “Here.” Oliver hands him the bear. “I can tell your miserable at this thing. I’m sorry for making you come.”

 

Jess takes the little bear, staring at it. “I’m not miserable, nothing with you is miserable.” He sighs, looking up. “I’m just worried about Rory. The night of the breakup, I could hear her crying in her room with her mom from down the hall. And I don’t think this friend thing is a good idea, especially with Lindsay rubbing it in Rory’s face that she’s with Dean now.”

 

“Look, I know you’re protective of Rory, but you have to trust that she knows what she’s doing. And, unfortunately, if this whole thing does come crashing down around her, just know that you’ll be there for her.” Jess knows he’s right, but he still hates that he has no control over the situation, only able to try and fix whatever fallout happens at the end of this shit-show.

 

Oliver gives him a kiss. “Thanks for the bear.” Jess says after they pull back.

 

Oliver’s cheeks are red, and not from the snow everywhere. “I know it’s kind of a stupid cliche, but I’ve always wanted to do the whole date thing where I win the stuffed animal and present it to my date. Although it was back when I was six, so it just seems super cheesy now. If you want, I’ll just-” He goes to take it back, but Jess keeps it out of reach.

 

“No take-backs. This is mine now. Besides, I like cheesy.”

 

“Jess, seriously. You don’t need to spare my feelings. I’ll give it to Clara, I’m sure she would like it.”

 

“I am being serious. I’ve already gotten attached. If you rip it from my hands now, both me and the bear will have separation anxiety. Do you want to be the root cause of mine and Theodore’s separation anxiety?”

 

“Who’s Theodore?”

 

“The bear. I thought he looked like a Theodore.” Jess holds the little white bear up, studying it. “What do you think? You can change the name if you want, but then he would have an identity issue on top of the separation anxiety you caused him. Do you really want that weighing on your conscience?”

 

Oliver chuckles, taking his hand as they start walking again. “Fine, for you and Theodore’s mental health, you can keep the bear.”

 

“Thank you.”

 

Oliver shakes his head, still laughing lightly. “God, you are so weird.”

 

“And yet you chose to date me.”

 

“Yeah, well, my blood sugar was low that day. I was delirious.”

 

“Too bad, no take-backs on me as well.”

 

“Or what? You’ll get separation anxiety?” He jokes.

 

“Nope.” Jess shakes his head.

 

“Really?” 

 

“Yup. Because I’ll always have Theodore.” Jess holds the bear up again, holding back a laugh.

 

“I should’ve just gave that thing to the kid. Hey, is my over talking thing really as annoying as her’s? Because that kid never shuts up.”

 

“Nah, it doesn’t bother me when you do it. Wanna know why?” Oliver nods. “Because when you start to talk too much, I can just do this.” Leaning over, Jess captures his lips with his own, going for a deeper kiss than the one earlier even though they’re still walking. They separate quickly as they nearly walk into someone, causing them to laugh.

 

“Sorry!” Oliver calls over his shoulder. The guy doesn’t respond, just grumbles about teenagers not being able to keep their hands to themselves these days.

 

“He may be right. Ollie, just think of the example we’re setting for Theodore.” Jess can’t help, but joke again.

 

Oliver slaps him on the shoulder. “Weirdo.” He snorts.


End file.
